
Holiday rentals with outdoor seating in Chesterton
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
Top-rated Holiday Houses with Outdoor Seating in Chesterton
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

Visit LakeMichigan Beach-Brewery-Casino-OutletMall
Explore the beautiful Indiana Dunes National and State Parks. Book your stay at this cozy, newly renovated 2 bedroom home centrally-located for all your adventures. Within 2 miles of beach, restaurants, brewery, winery, casino, concert venue, spa, botanical garden, splashpad, zoo, boat tours, kayak rental. Bonus trip: take the Southshore commuter train to Chicago for the day. Here, you can explore all the south shore of Lake Michigan has to offer then kick back at your home away from home. 💙

Newly Renovated with Finished Basement
This beautiful house is located near Lake Michigan in Northwest Indiana, less than 10 minutes from the expressway and toll road. There is a stainless steel kitchen, spa bathroom, finished basement and bar with sleeping capacity to accommodate two families. This is a smart home with Ring db, lights and thermostat controlled by your voice. We are less than an hour drive from downtown Chicago, and there are many great beaches nearby. Shopping and great dining options are also within a close drive.

Blue Birdhouse - Indiana Dunes
Welcome to The Birdhouse - Your Perfect Getaway! 🐦🌿 Nestled near the Indiana Dunes National Lakeshore, our cozy 2-bedroom, 1-bathroom home is perfect for families, couples, and nature lovers. Enjoy a pet-friendly, fully fenced yard, free parking for 2 vehicles, a fully equipped kitchen, laundry, and a BBQ grill with patio for outdoor dining. Minutes from Lake Michigan beaches, hiking trails, and local dining, it’s the ideal spot for beachgoers and adventurers. Book your stay today! 🌞🏖️🌳

House of Zen: Peaceful Modern Cabin on Tryon Farm
The House of Zen is an architect designed home situated in the woods, part of a sustainable farm community on 170 acres. Only an hour drive from Chicago, and close to Indiana Dunes National Park, it is the ultimate escape. The perfect getaway for couples, creatives and nature lovers who want some peace, quiet and space. Explore the farm trails & enjoy the wildlife and soothing sounds. Note: We have a 3 night minimum stay during summer, but open up 2 night stays 1-2 weeks before if possible.

South Shore Studio Apartment {National Park}
I have to warn you definitely not a hook up spot or party house!!! typically rise with rooster on this 5 acre country setting with a small fishing pond. 420 friendly .. Quiet hours are 11 -8 generally some music playing, musicians are welcome !! if you happen to book on a Sunday i host an Open Mic in my Barn every Sunday ..... pretty relaxed. Upon arriving, turn into the driveway, and then right into the yard. Apartment is upstairs, the door is open with the keys inside. ✌️

Duplex | Firepit | Game Room | Hot Tub-all year
You've found it – the perfect fun spot for your family beach vacation! Just a road trip away and less than half a mile from the beautiful beaches. Guests rave about the supplied beach accessories! You'll love the quiet, peaceful neighborhood close to the Michigan City's Washington Park beach, downtown, zoo, restaurants, outlet-mall shopping, and more. Grill outside; gather the family around the firepit , roast marshmallows, Smores Board provided. Play games like cornhole and board games.

Bro’s Place 6 mile drive to Indiana Dune’s
Welcome if you like country life Bro’s place is the place to be...watching the sheep, chickens and wildlife on you back deck making dinner on the grill with a full kitchen. Pick your own veggies outside the back door when in season. You will find a welcome basket with snacks, wine and homemade soap in bathroom fresh eggs from our chickens when available if your planning to visit our Beautiful Indiana Dunes you’ll find everything you need..chairs, towels, cooler Queen size sofa sleeper

"myhathouse" detached studio downtown Chesterton
Vaulted skylights allow natural light. Ksize bed. Couch opens into a full size bed. (DEEP cleaned to AirBnb COVID-19 disinfectant standards) Fully stocked kitchen, sm. bathroom w/ shower. Parking ft. of house, 1.5 M from Lake Michigan Shoreline, 2 blocks to 15th St. entry to Prairie-Dune Trail. European Market (May -Oct) each Saturday downtown. Fall season drives along U.S. HW 12 & 20 for foliage Winter day hikes, x-county skis trail, shopping trips to the Michigan City Outlet mall.

New Dunes Escape
Your family will be close to everything when you stay at this centrally-located place. Located just 3 minutes from the entrance of the Indiana Dunes National Park, 45 minutes from Chicago, 45 minutes from New Buffalo, MI , and 3 minutes from the Dunes Park South Shore Station, this completely remodeled home is the perfect place for a get-away. With free wifi, firepit with firewood, and a 4-seasons room, this house is the perfect place to relax after a great day swimming or hiking.

The Dune Den! Huge Yard/Firepit/Near Town+Dunes
Right in-between The Dunes National Park and downtown Chesterton, you will be close to everything when you stay at this centrally-located home. Things to look forward to: Less than 10 minutes to the Dunes and beaches or head 3 minutes the other way to downtown for food, drinks and plenty of small town fun. This charismatic home greets you with all new furniture, front porch, HUGE fenced yard, and local decor. You will fall in love with this family town so bring the kids!

Rainbows End 🌈 Plensa
Escape to a tranquil countryside cottage on a 20-acre farm. Enjoy breathtaking sunrises from the picture window, relax in lounge chairs, and gather around the fire pit and grill or take a trail walk down to the south branch of the Galien River. Just 10 minutes from Lake Michigan, and within 5 miles of a casino and a golf course, it's the perfect retreat for nature lovers and entertainment seekers. Book now and experience rural bliss with nearby attractions!

Cute Skylar: Valparaiso University ShortTerm
Welcome to Skylar's Relaxing Spot! This cozy one-bedroom on the second level features a queen-size bed, its own entrance, deck space, and building laundry facilities. Perfect for accessing downtown and Valpo University. Enjoy strong WiFi for remote work and relaxing movie nights on the TV. Located near Route 30 and I-49, it’s an hour from Chicago and 15 minutes from Indiana Dunes, close to malls, ice cream parlors, and great restaurants! ☺️
Popular amenities for Chesterton outdoor seating rentals
Holiday House Rentals with Outdoor Seating

National Park Nature Lover's Retreat

Entire Home Downtown Valparaiso!

Steps from the beach and a mile from National Park

UncleLarrysLakePlace HotTubKayaksPingPong

The Walnut House, Michigan Woods Retreat

The treehouse at Warren Dunes

In-town Lovely Home! Steps to Starbucks & Beach!

-The District 5 Schoolhouse-
Apartment rentals with outdoor seating

1Plant MOOD FREE Wi-Fi Parking Washer/Dryer

Relax - SW Mi Getaway/Hot Tub-Beaches & Wine Tours

Private Entrance Guest Suite on the River

ValpoVilla: Location, location, location!

Morton's Retreat Cozy 1 Bedroom Apartment

Second Floor Apartment sitting on Pine Lake

The Loft

Cozy Cottage by Lake MI&Dunes w/ private Hot Tub!
Condo rentals with outdoor seating

South Shore Dr Retreat

Updated Cottage Downtown, walk to Beach

2026 Open Perfect Location Condo Pools Walk to all

Nightingale Dunes - Modern beach town retreat

Live the marina life in New Buffalo!

Modern 2BR/2BA, 8 min Walk to ND, 2 Parking Spots

Uptown Penthouse on Pine:By Lake

Culver Cove Condo Right On Lake Max Unit 159
When is the best time to visit Chesterton?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $240 NZD | $253 NZD | $233 NZD | $230 NZD | $296 NZD | $314 NZD | $374 NZD | $331 NZD | $283 NZD | $299 NZD | $251 NZD | $256 NZD |
| Avg. temp | -3°C | -1°C | 4°C | 10°C | 16°C | 22°C | 25°C | 24°C | 20°C | 13°C | 6°C | 0°C |
Quick stats about holiday rentals with outdoor seating in Chesterton

Total holiday rentals
Explore 30 holiday rentals in Chesterton

Nightly prices starting at
Chesterton holiday rentals start at $99 NZD per night before taxes and fees

Verified guest reviews
Over 3,900 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
30 of Chesterton holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Chesterton rentals

4.8 Average rating
Chesterton stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
- Chicago Holiday rentals
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- Indianapolis Holiday rentals
- Downtown Chicago Holiday rentals
- Southern Indiana Holiday rentals
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- Columbus Holiday rentals
- Louisville Holiday rentals
- Cleveland Holiday rentals
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- Wisconsin River Holiday rentals
- Family-friendly rentals Chesterton
- Rentals with a fire pit Chesterton
- Rentals with a patio Chesterton
- Pet-friendly rentals Chesterton
- House rentals Chesterton
- Rentals with a washing machine and dryer Chesterton
- Cabin rentals Chesterton
- Rentals with outdoor seating Porter County
- Rentals with outdoor seating Indiana
- Rentals with outdoor seating United States
- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Grant Park
- Navy Pier
- 875 North Michigan Avenue
- Soldier Field
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- Warren Dunes State Park
- The Field Museum
- University of Notre Dame
- Wicker Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Oak Street Beach
- Frank Lloyd Wright Home and Studio
- Brookfield Zoo
- Museum of Science and Industry
- Willis Tower
- Washington Park Zoo
- Silver Beach Carousel




